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  • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
  • C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
  • C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
  • C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones
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  • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
  • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
  • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
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• • H—ELECTRICITY
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  • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
  • H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
  • H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
  • H01B1/121—Charge-transfer complexes

Definitions

• the invention relates to 4-substituted ⁇ -pyrone-5-carboxylic acid esters or 5-trifluoromethyl- ⁇ -pyrones and to 7-substituted naptho-1,4-quinone-6-carboxylic acid esters or 6-trifluoromethylnaphtho-1,4-quinones and to substituted butadienedicarboxylic acid esters.
• ⁇ -Pyrone-5-carboxylic acid esters are known, see, for example, H. Gault et al, C.r. Acad. Sci. Paris Ser. C, 266. pages 131-134 (1968).
• ⁇ -Pyrone-4,5-dicarboxylic acid diesters are described in U.S. Pat. No. 4,617,151.
• ⁇ -pyrone-5-carboxylic acid esters which are unsubstituted in the 3,6-position and substituted in the 4-position are not known. It has now been found that ⁇ -pyrones of this type can be obtained in a simple manner by reacting allenedicarboxylic acid esters with organometallic compounds to give propenedicarboxylic acid diesters which are substituted in the 2-position, reacting the latter with formic acid esters to give 1-alkoxymethylenebutadiene-2,4-dicarboxylic acid esters which are substituted in the 3-position and cyclizing the latter to give ⁇ -pyrones.
• the invention relates to compounds of the formula I ##STR2## in which R 1 is --CF 3 or --COOR 3 and R 3 is the radical of a C 1 -C 18 alcohol diminished by a hydroxyl group, and R 2 is --F, --Br, --Cl, --CN, --CF 3 , C 1 -C 18 alkyl, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkylthio, C 1 -C 18 alkylsulfonyl, C 6 -C 16 aryl, C 7 -C 24 alkaryl, C 7 -C 12 aralkyl, C 8 -C 24 alkaralkyl, C 6 -C 16 aryloxy, C 6 -C 16 arylthio, C 6 -C 16 arylsulfonyl, C 7 -C 24 alkaryloxy, C 7 -C 20 alkarylthio, C
• R 2 is --F, --Br, --Cl, --CF 3 , C 1 -C 18 alkyl, C 2 -C 18 alkenyl, C 1 -C 18 alkoxy, C 1 -C 18 alkylthio, C 1 -C 18 alkylsulfonyl, C 6 -C 10 aryl, C 7 -C 24 alkaryl, C 7 -C 12 aralkyl, C 6 -C 10 aryloxy, C 6 -C 10 arylthio, C 6 -C 10 alkylsulfonyl, C 7 -C 12 aralkyloxy, C 7 -C 12 aralkylthio or C 7 -C 12 aralkylsulfonyl.
• R 3 preferably contains 1-12 C atoms, especially 1 to 6 C atoms.
• R 3 can, for example, be linear or branched alkyl, C 5 cycloalkyl or C 6 cycloalkyl each of which is unsubstituted or substituted by C 1 -C 6 alkyl, or C 6 -C 12 aryl or C 6 -C 12 aryl-C x H 2x each of which is unsubstituted or substituted by C 1 -C 6 alkyl and in which x is 1 to 4.
• Aryl is preferably phenyl and x is preferably 1.
• R 3 is preferably C 1 -C 18 alkyl, particularly C 1 -C 12 alkyl and especially C 1 -C 6 alkyl. Some examples are methyl, ethyl, the isomers of propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl and octadecyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, benzyl, methylphenyl, dimethylphenyl, ethylphenyl, methylethylphenyl, t-butylphenyl and methylbenzyl. It is particularly preferable for R 3 to be methyl or ethyl.
• R 2 can be linear or branched and preferably contains 1 to 12 C atoms, particularly 1 to 6 C atoms and especially 1 to 4 C atoms.
• Examples are methyl, ethyl and the isomers of propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, heptadecyl and octadecyl and the corresponding alkoxy, alkylthio and alkylsulfonyl radicals.
• R 2 can be linear or branched and preferably contains 2 to 12 C atoms, particularly 2 to 6 C atoms.
• Some examples are vinyl, ethynyl, allyl, propargyl, prop-1-en-1-yl, but-1-en-4-yl, but-2-en-4-yl, pent-2-en-5-yl, hex-3-en-6-yl, but-2-yn-4-yl, pent-2-yn-4-yl, pent-2-yn-5-yl, hex-3-yn-5-yl and hex-3-yn-6-yl.
• R 2 as aryl or as a radical containing aryl is, for example, naphthyl or particularly phenyl.
• R 2 as alkaryl and the corresponding oxy, thio and sulfonyl radicals preferably contain 7 to 18 C atoms.
• R 2 as aralkyl and the corresponding oxy, thio and sulfonyl radicals preferably contain 7 or 8 C atoms.
• R 2 as alkaralkyl and the corresponding oxy, thio and sulfonyl radicals preferably contain 8 to 20 C atoms.
• R 2 as aryl or as a radical containing aryl is phenyl, phenoxy, phenylthio or phenylsulfonyl, C 1 -C 12 alkylphenyl, C 1 -C 12 alkylphenoxy, C 1 -C 12 alkylphenylthio or C 1 -C 12 phenylsulfonyl, C 1 -C 12 alkylphenyl--C n H 2n --, C 1 -C 12 alkylphenyl --C n H 2n O--, C 1 -C 12 alkylphenyl--C n H 2n S-- or C 1 -C 12 alkylphenyl--C n H 2n SO 2 --, or phenyl--C n H 2n --, phenyl--C n H 2n O--, phenyl--C n H 2n S-- or phenyl--C n H 2n --
• Some examples are phenyl, phenoxy, phenylthio, benzyl, benzyloxy, benzylthio, methylphenyl, methylphenoxy, methylphenylthio, methylbenzyl, methylbenzyloxy and methylbenzylthio.
• R 2 preferably contains 2 to 18, in particular 2 to 12, and especially 2 to 8, C atoms.
• the secondary amino can have the formula --NR 5 R 6 in which R 5 and R 6 independently of one another are linear or branched C 1 -C 18 alkyl, in particular C 1 -C 12 alkyl and especially C 1 -C 6 alkyl, cyclopentyl, cyclohexyl, phenyl, benzyl, C 1 -C 6 alkylphenyl or C 1 -C 6 alkylbenzyl, or R 5 and R 6 together are tetramethylene, pentamethylene or 3-oxa-1,5-pentylene.
• Some examples are dimethylamino, diethylamino, ethylmethylamino, dibutylamino, dioctylamino, methyldodecylamino, didodecylamino, methyloctadecylamino, phenylmethylamino, benzylmethylamino, pyrrolino, piperidino and morpholino.
• R 2 preferably contains 3 to 12 C atoms, in particular 3 to 8 C atoms.
• Alkyl and alkoxy groups have been mentioned above. Some examples are trimethylsilyl, triethylsilyl, dimethylethylsilyl, tributylsilyl, dimethylbutylsilyl, dimethyl-(1,1,2,2-tetramethylethyl)silyl, dimethyloctylsilyl, trimethoxysilyl and triethoxysilyl.
• a preferred group of compounds according to the invention is constituted by those in which R 2 is --F, --CN, --CF 3 , --Br, --Cl, C 1 -C 18 alkyl or C 2 -C 12 alkenyl, C 1 -C 18 alkoxy, C 1 -C 18 alkylthio, C 1 -C 18 alkylsulfonyl, phenyl, C 1 -C 12 alkylphenyl, phenyl--C n H 2n --, C 1 -C 12 alkylphenyl--C n H 2n --, phenoxy, phenylthio or phenylsulfonyl, C 1 -C 12 alkylphenoxy, C 1 -C 12 alkylphenylthio or C 1 -C 12 alkylphenylsulfonyl, phenyl--C n H 2n --O--, phenyl--C n H 2n --S-- or
• R 2 is --F, --Cl, --Br, --CF 3 , C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 1 -C 12 alkylthio, benzylthio or C 1 -C 12 alkylbenzylthio or secondary amino having 2 to 12 C atoms.
• the invention also relates to a process for the preparation of compounds of the formula I, which comprises cyclizing a compound of the formula II ##STR3## in which R 2 and R 3 are as defined above and R 4 is C 1 -C 4 alkyl, in the presence of a strong, anhydrous acid, to give a compound of the formula I.
• R 4 is particularly methyl or ethyl.
• the invention also relates to the compounds of the formula II. They can be prepared in a manner analogous to the process described in U.S. Pat. No. 4,617,151 by reacting propene-1,3-dicarboxylic acid diesters of the formula III ##STR4## with formic acid esters HCOOR 4 in the presence of TiCl 4 or an alkali metal hydride or alcoholate.
• suitable alkali metals are Li, Na and K and Examples of alcohols are C 1 -C 4 alkanols, for example methanol and ethanol.
• the compounds of the formula III can be prepared by various methods.
• the starting compound is, for example, the known ketodicarboxylic acid diester of the formula IV ##STR5##
• Compounds of the formula III in which R 2 is an alkoxy radical are obtained by enolization with alkylating agents, for example dialkyl sulfates, orthoformic acid esters in the presence of FeCl 3 , or alkyl halides.
• R 2 is a hydrocarbon radical
• an inorganic copper salt for example copper(I) halides or in particular CuCN
• Compounds of the formula III substituted by secondary amines are also obtained by direct reaction with secondary amines.
• the reaction with R 2 Z is advantageously carried out in a polar, aprotic solvent. Examples are ethers, especially diethyl ether, dibutyl ether, tetrahydrofuran, dioxane or ethylene glycol diethyl ether.
• the reaction temperature is advantageously -20° to -100° C.
• the cyclization of compounds of the formula II can also be carried out by the process described in specification U.S. Pat. No. 4,617,151. It is advantageous to carry out the cyclization using anhydrous formic acid or polyphosphoric acid without a solvent.
• the temperature for this reaction is advantageously 50° to 250° C.
• the compounds of the formula I can be reacted with benzo-1,4-quinone to give naphthoquinones of the formula VI ##STR7## in which R 1 and R 2 are as defined in formula I.
• the invention also relates to these naphthoquinones.
• R 2 in formula VI is --CF 3 , F, --Cl, --Br, C 1 -C 18 alkyl, C 1 -C 18 alkoxy, C 1 -C 18 alkylthio, C 1 -C 18 alkylsulfonyl, phenoxy, phenylthio, phenylsulfonyl, C 1 -C 12 alkylphenoxy, C 1 -C 12 alkylphenylthio, C 1 -C 12 alkylphenylsulfonyl, benyloxy, benzylthio, benzylsulfonyl, C 1 -C 12 alkylbenzyloxy, C 1 -C 12 alkylbenzylthio or C 1 -C 12 alkylbenzylsulfonyl.
• R 1 is --CH 3 or --COOR 3 and R 2 is --CF 3 , --F, --Cl, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 1 -C 12 alkylthio, C 1 -C 12 alkylsulfonyl or benzylthio and R 3 is C 1 -C 4 alkyl.
• CT complexes can be prepared from such chalkogenated tetracenes by means of electron acceptors. They can be attached to polymers, for example incorporated into polymers as side groups (cf. U.S. Pat. No. 4,617,151) by means of their functional groups.
• the CT complexes are also suitable for the production of, for example, antistatic coatings of photographic film elements, magnetic tapes, electrophotographic film elements and electronic components (see U.S. Pat. No. 3,634,336).
• the chalkogenated tetracenes also exhibit electrochromic properties; they can be used for electrochromic displays. They are also suitable for use as laser-optical data storage [Nach. Chem. Techn. Lab. 35, pages 255 et seq. (1987)] and as anode material in organic solid state batteries (EP-A 0,090,598).
• CT complexes of unsubstituted or substituted tetrathiotetracenes or tetraselenotetracenes can also be incorporated into thermoplastic, thermosetting or elastomeric polymers in order to achieve antistatic properties.
• tetrathiotetracenes or tetraselenotetracenes are advantageously effected, for example, by dissolving these tetrathiotetracenes or tetraselenotetracenes, together with a soluble polymer or a precursor thereof and an electron acceptor, for example an agent which forms halogen (organic halogenated compounds, for example bromoform, trichlorobromomethane, tetrabromomethane, hexachloropropane, perchlorobutadiene, 1,3-dichloro-2-butene, 1,4-dichloro-2-butene, 1,4-bis-(trichloromethyl)-benzene, iodoacetonitrile, iodoform, tetrachloroethylene, perchlorocyclobutadiene, N-chlorosuccinimide, N-bromosuccinimide or N-iod
• composition formed contains, in the polymer, a network of needle-shaped crystals of the CT complex, if the chalkogenated tetracene is unsubstituted or contains small substituents (for example F, CH 3 or CF 3 ).
• Compositions of this type exhibit a high electrical conductivity.
• the compounds of the formula I are valuable diene components for DielsAlder reactions, for which a variety of dieneophiles can be used. If substituted or unsubstituted 1,4-quinones are used, for example benzo-1,4-quinone, naphthalene-1,4-quinone or anthracene-1,4-quinone, quinones enlarged by a ring are obtained (see, for example, EP-A 0,195,743).
• Substituted naphthacene-5,12-diones can also be obtained directly by reacting substituted or unsubstituted naphthalene-1,4-quinones with benzocyclobutenes which are substituted in the 1-position and 2-position by bromine and/or iodine.
• Anthraquinones and naphthacene diones can be used, for example, as photosensitizers (cf. U.S. Pat. No. 3,941,759) or photoinitiators for the polymerization of ethylenically unsaturated compounds, in particular naphthacene-5,12-diones which are at least substituted by a thio radical in the 2-position.
• Naphthacene quinones can also be used in electrochromic display elements (Japanese Preliminary Published Specification 61-43,680).
• the reaction mixture is stirred at room temperature for 24 hours and is then introduced into 150 ml of CH 2 Cl 2 and 100 ml of saturated KHCO 3 solution. After stirring for 30 minutes, the precipitated titanium salt is filtered off. The CH 2 Cl 2 solution is separated from the water in the filtrate. The CH 2 Cl 2 phase is washed with water, dried with Na 2 SO 4 and evaporated, and residual N-methylmorpholine is removed at 100° C./1.3 mbar. The oily residue is filtered through 150 g of SiO 2 (mobile phase CH 2 Cl 2 ; 0.3 bar excess pressure). The crude product obtained is chromatographed (silica gel; mobile phase: CH 2 Cl 2 ). 1.95 g (43.5%) of a pale yellow oil are obtained.
• reaction mixture is then stirred at room temperature overnight and is then introduced into a mixture of 1000 ml of CH 2 Cl 2 and 2000 ml of saturated NaHCO 3 solution. After being stirred for 30 minutes, the mixture is filtered. The CH 2 Cl 2 phase of the filtrate is separated from the aqueous phase, washed again twice with 300 ml of water, dried with Na 2 SO 4 and concentrated in vacuo. 47.66 g (94%) of an orange oil are obtained.
• the residue is suspended in 200 ml of CH 2 Cl 2 , 200 ml of water containing 11 g of NaHCO 3 are added and the mixture is filtered after being stirred for 1 hour. The two phases of the filtrate are separated and the organic solution is concentrated under a water pump vacuum. The residue is filtered through a column of 35 g of silica gel (mobile phase: CH 2 Cl 2 ). 1.92 g (69.6%) of an oily product remain after the mobile phase has been removed by distillation.
• distillation residue (29 g) is crystallized from a mixture of 12 ml of diethyl ether and 10 ml of hexane at -20° C. Yield 22.79 g (42%), melting point: 38°-39° C.
• a solution of 130.41 g (0.69 mol) of TiCl 4 in 170 ml of CCl 4 is added dropwise, with stirring, to 1380 ml of THF. During this addition, the temperature is kept at 0° C. by cooling.
• First 36.72 g (0.17 mol) of ethyl 3-ethoxyglutaconate and then 51.06 g (0.69 mol) of ethyl formate are introduced and, finally, 139.38 g (1.38 mol) of N-methylmorpholine in 241 ml of THF are added dropwise at 0° C. in the course of 0.5 hour.
• the reaction mixture is stirred overnight at room temperature and is then introduced into a solution of 150 g of NaHCO 3 in 1200 ml of H 2 O and 1200 ml of CH 2 Cl 2 , and the mixture is stirred for 2 hours.
• the precipitated titanium dioxide is filtered off with suction.
• the filtrate is then extracted with 3 ⁇ 300 ml of methylene chloride.
• the combined methylene chloride extracts are dried with Na 2 SO 4 and concentrated.
• the crude product which remains is chromatographed over a column filled with 1300 g of silica gel 60 (mobile phase 19:1 CH 2 Cl 2 /acetone, 0.3 bar excess pressure). 31.9 g (67.6%) of an oily product are obtained after the mobile phase has been removed.
• a mixture of tetrabutylammonium dihydrogentrifluoride (prepared from 30 mmol of tetrabutylammonium fluoride, KF and HF), 20 ml of 1,2-dichloroethane and 15 mmol (2.76 g) of diethyl allenedicarboxylate is heated under reflux for 1 hour. The mixture is then diluted with methylene chloride and washed slowly with ice water, sodium bicarbonate and ammonium chloride solution, dried with Na 2 SO 4 and evaporated. The crude product is flash-filtered over 50 g of silica gel using 500 ml of 4:1 hexane/ethyl acetate and distilled under a high vacuum. 1.79 g (59% of theory) of the desired product are obtained; boiling point: 50°-55° C./0.06 mbar.
• THF tetrahydrofuran
• the reaction mixture is stirred for 17 hours at room temperature and is then stirred into a mixture of 50 ml of saturated KHCO 3 solution and 100 ml of CH 2 Cl 2 .
• the precipitated titanium salt is filtered off with suction, and the organic phase is separated off from the aqueous phase.
• the aqueous phase is extracted once more with 100 ml of CH 2 Cl 2 , and the combined organic phases are dried with Na 2 SO 4 and concentrated.
• the distillation residue is freed from excess N-methylmorpholine at 85° C./1.3 mbar, and the residue is chromatographed over 150 g of SiO 2 (mobile phase 19:1 CH 2 Cl 2 /acetone). This gives 1 g (77% of theory) of the product (an orange oil).
• a solution of 4.53 g (0.024 mol) of TiCl 4 in 6 ml of CCl 4 is added dropwise to 48 ml of THF with ice cooling (0°-5° C).
• First 1.77 g (0.024 mol) of formic acid ester and then 1.58 g (0.006 mol) of diethyl 3-methylsulfonylpent-2-enedicarboxylate are added dropwise at the same temperature, with stirring.
• 4.86 g (0.048 mol) of N-methylmorpholine in 8.5 ml of THF are added at 0°-5° C. in the course of 1 hour.
• the reaction mixture is then stirred for 20 hours at 25° C., diluted with 100 ml of CH 2 Cl 2 and poured into 30 ml of saturated KHCO 3 solution.
• the titanium salt is filtered off with suction and the organic phase is separated from the filtrate.
• the aqueous phase is extracted with a further 50 ml of CH 2 Cl 2 .
• the combined CH 2 Cl 2 extracts are washed with saturated NaCl solution, dried with Na 2 SO 4 and concentrated.
• the distillation residue is chromatographed (200 g of silica gel; mobile phase 19:1 CH 2 Cl 2 /acetone). This gives 1.17 g (60.94%) of the product.

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